Cesium carbonate → HCID 90020436, compound

HRID 2200189Notes

Reaction equation

HRID 2200189 reaction equation
Cl[C:2]1C=C[C:5]([NH:8][C:9](=O)OC2C=CC=CC=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])F.[C:22](=[NH:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:36]([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[F:21][C:18]([C:3]1[CH:2]=[CH:9][N:8]=[C:5]([N:35]=[C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:4]=1)([F:20])[CH3:36]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 13412531HCID 13412531, compound

Product 1

HCID 90020436HCID 90020436, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Add the compound obtained in Step 1 (1.21 g, 6.81 mmol), benzophenone imine (1.83 g, 10.22 mmol), Cs2CO3 (4.43 g, 13.6 mmol) to 1,4-dioxane (15 mL), then under N2, add BINAP (635 mg, 1.02 mmol), Pd2(dba)3 (623 mg, 0.68 mmol), stir the reaction at 120° C. under N2 atmosphere for 15 hrs. Cool to room temperature; filter off the solid, concentrate the filtrate under reduced pressure to give a crude residue. Purification by chromatography (silica gel, EtOAc:PE=1:3) affords the target compound (1.68 g, 76.3%). MS: (M+1): 323.2.

Workup

  1. customthe reaction at 120° C. under N2 atmosphere for 15 hrs
  2. filtrationfilter off the solid
  3. concentrationconcentrate the filtrate under reduced pressure
  4. customto give a crude residue
  5. customPurification by chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-663f38b1a7a64d57b81cf5ff704ee750
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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